The Internet is increasingly used as a source for information and knowledge. In the context of information gathering on health-related issues via Internet, healthcare institutions such as health insurance companies are important information providers. In this context the emergence and broad adoption of Web 2.0 technologies can be observed. As health insurance companies play a highly relevant role in the German healthcare system, we conduct a comparative analysis. The following questions are of interest: (1) How many German health insurance providers apply Web 2.0 technologies? (2) How has the application of Web 2.0 technologies in the German health insurance landscape changed? (3) Does diffusion and growth indicate an increasing fashion wave in this context? According to an adapted conceptual model for Web 2.0 use, all private and public health insurances were analyzed according to the use of Web 2.0 technologies. Our results show that public health insurers provide more Web 2.0 technologies than private health insurance providers. The inter-temporal analysis between 2009 and 2010 shows some significant changes for the diffusion of Web 2.0 technologies.